Hydrochloric Acid → HCID 68718600, compound

HRID 2266417Notes

Reaction equation

HRID 2266417 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([S:11][CH2:12][CH2:13][N:14]2[C:18](=[O:19])[CH2:17][CH2:16][C@@H:15]2[CH2:20][O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[S:9][CH:10]=1)=[O:5])C.CO.[OH-].[Na+].Cl>O1CCCC1>[Si:22]([O:21][CH2:20][C@H:15]1[CH2:16][CH2:17][C:18](=[O:19])[N:14]1[CH2:13][CH2:12][S:11][C:8]1[S:9][CH:10]=[C:6]([C:4]([OH:5])=[O:3])[N:7]=1)([C:25]([CH3:28])([CH3:26])[CH3:27])([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 68717872HCID 68717872, compound

Product 1

HCID 68718600HCID 68718600, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(2-((2R)-2-(t-butyldimethylsilyloxymethyl)-5-oxopyrrolidin-1-yl)ethylthio)-1,3-thiazole-4-carboxylic acid ethyl ester (240 mg; the compound described in Reference Example 17 of WO03/74483) in tetrahydrofuran (4 mL)-methanol (2 mL) was added 2N aqueous sodium hydroxide solution (2 mL) at room temperature and the solution was stirred for 1 hour. The reaction solution was acidified with dilute hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated to give the title compound (240 mg) having the following physical data.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4a7fad36424a4189af0393dfe198a97a
Source dataset
uspto-grants-2010_12
Patent number
US07858650B2

Reaction notes

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